1. Download cygwin from http://cygwin.com/. Run the setup program and select the packages you want. The simplest thing to do is to get the default packages that are selected for you by the installer, plus “cygrunsrv” from the admin category and “openssh” from the net category. I found installing cygwin to be the easiest part of the process, and if you get stuck there’s lot’s of great help out there…

2. Edit C:cygwincygwin.bat. Make sure it contains the following setting for the CYGWIN environmental variable:

set CYGWIN=binmode tty ntsec

2. Start a cygwin bash shell. If cygwin installed correctly, you should be able to find it in start->programs->cygwin.

3. Make sure cygrunsrv is installed by typing “cygrunsrv -S sshd”. This is the command that will start the sshd server, but that’s not installed yet. If you get an error from cygrunsrv like “service does not exist” then you’re on the right track. If you get “command cygrunsrv not found”
then go back over your install and make sure you get cygrunsrv.

4. Again from the bash shell, run ssh-host-config. Answer yes to the key generation questions. I found it easier not to use privilege separation. Answer yes to install as a service.

5. Start sshd with “cygrunsrv -S sshd” (“cygrunsrv -E sshd” shuts it down). At this point you should also have “Cygwin sshd” available as a service that you can start and stop from start->control panel->administrative tools->computer management – go to the services and applications->services list.

6. If all that went well, you should be able to ssh to the server(“ssh localhost -l loginName”). At this point only user accounts that existed before your cygwin install and had administrator access will work. This and the next step were the biggest gotchas for me in this whole game.

7. To enable a user to log in via ssh: You should know that sshd looks for information in the comments field of /etc/passwd and coordinates it with NT permissions. This was mentioned but not explained in the howtos I read.

Here’s how make it work: First, create the NT user and make them part of the administrators group.

Next, use the mkpasswd command to format a special passwd entry for that user. You can look at the output with the command “mkpasswd -l”. Then either cut and paste the info you need into your /etc/passwd file, or use the command “mkpasswd -l > /etc/passwd”.

This second will overwrite your existing passwd file. No matter what you do, make a copy of /etc/passwd before making any changes.

Create home directories for your users with the following commands:
“mkdir /home/userLogin”
“chown userLogin /home/userLogin”

Sshd only reads /etc/passwd once when it starts, so stop and start the server after you make changes to /etc/passwd.

I take it the mkgroup command does the same thing for /etc/group as mkpasswd does for /etc/passwd; I never needed to use it.

The openssl toolkit is used to generate an RSA Private Key and CSR (Certificate Signing Request). It can also be used to generate self-signed certificates which can be used for testing purposes or internal usage.

The first step is to create your RSA Private Key. This key is a 1024 bit RSA key which is encrypted using Triple-DES and stored in a PEM format so that it is readable as ASCII text.

Once the private key is generated a Certificate Signing Request can be generated. The CSR is then used in one of two ways. Ideally, the CSR will be sent to a Certificate Authority, such as Thawte or Verisign who will verify the identity of the requestor and issue a signed certificate. The second option is to self-sign the CSR, which will be demonstrated in the next section.

During the generation of the CSR, you will be prompted for several pieces of information. These are the X.509 attributes of the certificate. One of the prompts will be for “Common Name (e.g., YOUR name)”. It is important that this field be filled in with the fully qualified domain name of the server to be protected by SSL. If the website to be protected will be https://public.akadia.com, then enter public.akadia.com at this prompt. The command to generate the CSR is as follows:

One unfortunate side-effect of the pass-phrased private key is that Apache will ask for the pass-phrase each time the web server is started. Obviously this is not necessarily convenient as someone will not always be around to type in the pass-phrase, such as after a reboot or crash. mod_ssl includes the ability to use an external program in place of the built-in pass-phrase dialog, however, this is not necessarily the most secure option either. It is possible to remove the Triple-DES encryption from the key, thereby no longer needing to type in a pass-phrase. If the private key is no longer encrypted, it is critical that this file only be readable by the root user! If your system is ever compromised and a third party obtains your unencrypted private key, the corresponding certificate will need to be revoked. With that being said, use the following command to remove the pass-phrase from the key:

At this point you will need to generate a self-signed certificate because you either don’t plan on having your certificate signed by a CA, or you wish to test your new SSL implementation while the CA is signing your certificate. This temporary certificate will generate an error in the client browser to the effect that the signing certificate authority is unknown and not trusted.

To generate a temporary certificate which is good for 365 days, issue the following command: